Stereochemical study of a Lewis acid-promoted reaction of 2-silyloxypyrrole with aliphatic and aromatic aldehydes

被引：15

作者：

Uno, H

Nishihara, Y

Mizobe, N

Ono, N

机构：

[1] Ehime Univ, Adv Instrumentat Ctr Chem Anal, Matsuyama, Ehime 7908577, Japan

[2] Ehime Univ, Fac Sci, Dept Chem, Matsuyama, Ehime 7908577, Japan

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 1999年 / 72卷 / 07期

关键词：

D O I：

10.1246/bcsj.72.1533

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In the presence of BF3 OEt2, the reaction of 1-t-butoxycarbonyl-2-t-butyldimethylsiloxypyrrole with aliphatic and aromatic aldehydes in ether occurred stereoselectively to give the corresponding erythro and threo isomers, respectively, while a similar reaction in the presence of SnCl4 showed completely opposite selectivity. The transition states leading to the major isomers are discussed.

引用

页码：1533 / 1539

页数：7

共 20 条

[1] And in the end ... a terminal flower!
Battey, N
[J]. TRENDS IN PLANT SCIENCE, 1996, 1 (06) : 167 - 168
[2] Asymmetric routes towards polyfunctionalized pyrrolidines: Synthesis and reactivity of a chiral silyloxypyrrole.
Baussanne, I
Royer, J
[J]. TETRAHEDRON LETTERS, 1996, 37 (08) : 1213 - 1216
[3] FURANOLATE-BASED STRATEGY FOR SEQUENTIAL 2,3,4-TRISUBSTITUTION OF BUTENOLIDE - TOTAL SYNTHESIS OF NOSTOCLIDE-I AND NOSTOCLIDE-II
BOUKOUVALAS, J
MALTAIS, F
LACHANCE, N
[J]. TETRAHEDRON LETTERS, 1994, 35 (43) : 7897 - 7900
[4] REGIOSTEREOSELECTIVITY AND DIASTEREOSELECTIVITY IN ALDOL REACTIONS OF CYCLOPENT-2-ENONE, 2-(5H)FURANONE AND THEIR DERIVED TRIMETHYLSILYLOXYDIENES
BROWN, DW
CAMPBELL, MM
TAYLOR, AP
ZHANG, X
[J]. TETRAHEDRON LETTERS, 1987, 28 (09) : 985 - 988
[5] GASIRAGHI G, 1995, SYNTHESIS-STUTTGART, P607
[6] MITHRIL - AN INTEGRATED DIRECT-METHODS COMPUTER-PROGRAM
GILMORE, CJ
[J]. JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1984, 17 (FEB) : 42 - 46
[7] DIASTEREOSELECTIVITY IN THE DIRECTED ALDOL CONDENSATION OF 2-TRIMETHYLSILOXYFURAN WITH ALDEHYDES - A STEREODIVERGENT ROUTE TO THREO-DELTA-HYDROXY-GAMMA-LACTONES AND ERYTHRO-DELTA-HYDROXY-GAMMA-LACTONES
JEFFORD, CW
JAGGI, D
BOUKOUVALAS, J
[J]. TETRAHEDRON LETTERS, 1987, 28 (35) : 4037 - 4040
[8] KOBAYASHI S, 1995, SYNTHESIS-STUTTGART, P1195
[9] KOBAYASHI S, 1993, SYNLETT, P911
[10] KOBAYASHI S, 1995, YUKI GOSEI KAGAKU KY, V53, P370

← 1 2 →